The 15 Biggest Mistakes in Hip Hop History

We look back at some of the biggest mistakes in hip hop history: From Diddy to Suge, we count down some of the most questionable decisions, biggest mistakes & lack of judgement calls in hip hop history.

15. Rick Ross Denying Parole Officer Accusations Before Rick Ross was writing rhymes and creating street anthems, he was writing citations and patrolling the streets. When a 2009 Smoking Gun report emerged exposing Rozay’s past as a C.O, Ross quickly denied the allegations despite an overwhelming amount of evidence. Instead of burying the topic right away, Ross let it linger and he ultimately became a laughing stock for that period of time. (Although he’s recovered nicely since)

14.Nelly – Tip DrillFor most Americans their problems can be traced back to swiping their credit cards on multiple occasions,
but for Nelly it took just 1 infamous swipe to forever alter his career. In his controversial, yet entertaining 2004 X-rated “Tip Drill” video, Nelly took it upon himself to swipe his American Express (or was it a Visa?) down a stripper’s ass, which led to an uproar from females all across the country. Since 99% of Nelly’s fan base wears high heels, we don’t think it was wise of him to piss off damn near every female rights group imaginable. The swipe led to boycotts, corporate advertisers pulling ads in-which Nelly was featured on and more. Nelly’s career hasn’t been the same since.

13.Any Artist that Signs to Bad Boy RecordsA sports franchise that screws up free agent signings, ruins young careers, never pays their employees, and has been irrelevant for the better part of a decade would be called the Los Angeles Clippers, but in the music industry, that unflattering description belongs to Bad Boy Records. Contrary to popular belief, Bad Boy isn’t cursed; it’s just run by an egomaniac that would rather showcase himself than his artists. Any artist that wants to be a star, and stay a star, and not have to worry about the executive producer tryna be all in the videos, all on the records, dancing, don’t go to Bad Boy Records, word to Suge Knight.

12. 50 Cent Black Balling Himself After years of bullying his peers, criticizing and making a mockery of artists beneath him, 50 finds himself in a precarious position in which he’s struggling to produce any type of buzz for his free-falling music career. He burned a lot of bridges on his rise to the top and it’s coming back to haunt him. These days 50 releases a lot of music via his twitter page, but one has to ask, if he releases music and nobody hears it, did he really release music? On his quest to get rich or die trying, he essentially black-balled himself, and now fans are hoping he would stop trying to make music.

11. Hot 97 Giving Funk Master Flex a Radio ShowFlex is a legendary DJ who was one of the biggest influences back in the 90s, however, he’s also one of the biggest dick riders in hip hop history. Flex is a male-cheerleader who annoyingly giggles, instigates and kisses every rappers ass that appears on his radio show. There’s only 3 people who enjoy his radio show, and that’s the program director, the radio engineer and Funkmaster Flex, and we’re told all 3 are the same person.

10. Lil B Deciding to RapTitle is self-explanatory

9. Jay Z Calling Out Nas @ Summer Jam 2001f we learned anything from the ignorant WorldStar fight videos, it’s that the aggressor in a fight usually ends up taking a loss. And in this case, Hov was the loud ostentatious one showing off around his peers, Nas was the quite individual who paid the aggressor no mind and wanted no parts of the fight, until Jay threw the first punch. And Nas, seemingly out of nowhere unleashed a hail of fury that subsequently put an asterisk on Jay’s previously unblemished record.

8. Signing to Aftermath Records.Dre’s former label Death Row Records was the destination for artists to, well, die, literally. Now Dre’s Aftermath Records is the destination where artists go to, well, die; figuratively. Just check the stats, Aftermath was established in 1996 and there’s been less than 10 albums released while having at least 50 artists signed in that period of time.

7. Signing to Death Row RecordsSigning to Suge’s nemesis Bad Boy Records would leave you broke, irrelevant and bitter, but at least you’d still be alive. We’re not implying Suge Knight did a lot of evil stuff himself, we’re implying Suge Knight had goons to do the evil stuff on his behalf.

*Note* (Opinions expressed in this particular post concerning Suge Knight & Death Row records are solely of that of the writer, and doesn’t reflect those of HH365 Media Group)

6. Soulja BoyRefer back to #10

#5 Lil Wayne’s Wardrobe @ MTV Awards 2011So we know that the “Goblin” thing has kind of caught on, and we’re supposed to think it’s cool to dress like a complete moron if you’re expressing your inner martian. But when you emerge from a tunnel wearing women’s pants and crooning your softest song to date, it doesn’t make us think of you as a goblin. It makes us think of you as a prom queen.

4. Drake Beefing with Common Beefing with Common isn’t a wise thing to do, just ask Ice Cube. That beef in 97’ ended when Cube called Minister Farrakhan to help intervene and squash the beef. However, being that Drake is half-white & a Jew were not sure Farrakhan will assist this time around. So Drake should just lay low until till things simmer down so he can return to doing what he does best, which is singing and making the same song, over and over again.

3. Signing Shyne to Def JamQuick Update on some of the players involved in the 1999 Shooting in New York.
-Shyne serves nearly 10 years in prison for Diddy.
-L.A. Reid signs Shyne
-Shyne releases some of the worst music of all time, in any genre.
-The U.S. quickly deports Shyne to Israel, presumably after hearing his music.
-Def Jam Fires L.A., and he heads to X-Factor
-J-Lo gets divorced
-The NYC man who instigated the 99′ shooting, was found dead earlier this year outside of a Manhattan nightclub.
-Meanwhile Diddy is somewhere laughing at one of his beach houses in Miami.

2. Vibe Magazine’s 1996 East vs West CoverAlthough there were several publications that fed into the beef between Death Row & Bad Boy, Vibe was the biggest urban media outlet that continually accentuated and fueled fire into the beef. They coined the “East vs West” term and turned a dispute between two record labels, into an all out coastal war. Even the former EIC Kevin Powell now regrets the cover and the stuff they did. Sure the beef would have probably still went on with or without the cover, but it sure didn’t help matters.

1. Twitter & Hip HopFor a genre that rose fully-formed from the concrete Hip-Hop has started to seem awful soft these days. Partly that’s a good thing; expansion of subject matter leads to more diverse artists saying all kind of different things. But it also leads to some really lame shit. And the lamest of the lame happenings in current hip-hop is the twitter beef. Because there’s nothing at risk and there’s no skill involved. All the drama of the hip-hop battle, where dudes clowned their enemies through rhyme, all the tension of seeing two men compare skill face to face has disappeared, replaced by inane insults hurled safely through modems. In fact, the wackest participant often wins the twitter beef, simply because they’re lame enough to keep going when the realer dude has better stuff to do with his time. We don’t even hear good diss songs anymore because rappers are letting a website represented by a cute little bird do all their talking for them. Stop this trend. If you hate a dude, write a sixteen or a verse or a song about how much he sucks. Don’t condense it into 140 characters. Negro please